Title: Organic Chemistry
1Organic Chemistry
2Organic Families Alcohols
Methyl, an alkyl group
Methanol, an alcohol (alkly hydroxyl)
Methane
3Organic Families Alcohols
Ethanol
4Organic Families Alcohols
2-propanol (isopropyl alcohol rubbing alcohol)
1-propanol
Your nose can tell the difference!
5Organic Families Alcohols
1-pentanol
2-pentanol
3-pentanol
6Organic Families Alcohols
Primary
Secondary
Tertiary
7Some Alcohols at Home
Are generally toxic if ingested!
8Organic Families Alcohols
- Alcohol a hydroxyl in place of -H in an alkane
- General formula R-OH ( R is any alkyl group)
- Classes
- Primary one alkyl group on CH2OH
- Secondary two alkyl groups on CH2OH
- Tertiary three alkyl groups on CH2OH
- Alcohol of 1-4 carbons very soluble in water of
5 -7 carbons slightly soluble in water of 8 or
more carbons are not soluble in water
9Organic Families Alcohols
- Hydroxyl group with oxygen and hydrogen can form
hydrogen bonds so may make an organic compound
polar - Hydroxyl group is important in sugars, starches
and steroids including cholesterol
10Organic Families Phenols
Phenol benzene ring with hydroxyl
Menthol
11Some Phenols at Home
12Organic Families Phenols
- Phenol a hydroxyl in place of -H on a benzene
ring - In water, phenols ionize slightly as a weak acid
- Concentrated solutions of phenols are corrosive
13Organic Families Thiols
-SH
-OH
Thiol (methanethiol)
Alcohol (methanol)
14Organic Families Thiols
CH3-SH in osyters and cheese
CH3-CH2-CH2-SH in onions
CH2CH-CH2-SH in garlic
-SH gives us the strong odors of skunks and these
foods
15Organic Families Thiols
- Thiol a -SH in place of -OH
- Short-chain thiols have a disagreeable odor
- Important in proteins
16Organic Families Ethers
Dimethyl ether
Ether Group
Ethyl methyl ether
Methyl phenyl ether
17Organic Families Ethers
- Ether contains an oxygen atom that is attached
by single bonds to two carbons - Has oxygen so can hydrogen bond with water
- Diethyl ether was used as an anesthetic for more
than a hundred years it is volatile and
flammable - Newer anesthetics have ether group that has side
effects in humans so use halothane
18Hydrogen Bonding in Organics
Ethers do not hydrogen bond to each other
Hydroxyls hydrogen bond to each other
19Hydrogen Bonding in Organics
Hydroxyls hydrogen bond to water
Ethers hydrogen bond to water
20Organic Families Ethers
- Short-chain ethers are soluble in water like
alcohols because of hydrogen bonding - Dimethyl ether is soluble in water
- Diethyl ether is slightly soluble in water
- Ethers have boiling points more like alkanes
because ethers do not hydrogen bond to each other
- Need more energy to break hydrogen bonds
- Alcohols have higher boiling points than alkanes
and ethers
21 Organic Families Carbonyl Group
Dipole to dipole bond (increases boiling point)
Strong polarity (water soluble)
Carbon double-bonded to oxygen (responsible for
wide variety of flavors and odors)
22Organic Families Aldehydes and Ketones
O CH3 - CH2 - C - H or CH3 - CH2 - C -
OH
O CH3 - C - CH3 or CH3
CO - CH3
Aldehyde carbonyl attached to and end C
(carbonyl has a hydrogen)
Ketone carbonyl not on an end C
(carbonyl attached to two alkyls or aromatic
rings)
23Some Carbonyls in the Home
Aldehydes
Ketones
24Organic Families
- Aldehydes and ketones have similar properites
polar 1 to 4 Cs are water soluble - Also very different
- Tollens test AgNO3 in ammonia oxides aldehydes
but not ketones - Primary alcohol oxides to aldehyde secondary
alcohol oxides to ketone - Aldehydes oxidize to carboxylic acids ketones do
not oxidize
25Organic Families Aldehydes
Methanal (formaldehyde)
Ethanal (acetaldehyde)
Propanal
26Organic Families Aldehydes
- Formaldehyde colorless gas with pungent odor
- Reactant in sythesis of polyers
- Formulin (40 formaldehyde in water) is a
germicide - Benzaldehydes give odor to cinnamon, almond and
vanilla - Aldehydes are used to flavor food and as
fragrances in perfumes
27Organic Families Ketones
Propanone (acetone)
Butanone
Cyclopentanone
Butanedione (butter flavor)
28Organic Families Ketones
- Acetone colorless liquid with mild odor
- In cleaning fluids, paint remover, nail polish
remover, rubber cement - Produced in the body when high amount of fats are
burned for energy gives fruity odor to breath - Dihydroyacetone in sunless tanning lotions
darkens the skin - Butanedione gives the flavor of butter
29Why does vanilla appear more than once?
?
Ether
?
Phenyl
?
Hydroxyl
?
Aldehyde